Methanol → N-(3-ethyl-1-((1-(4-methoxybenzyl)-1H-pyrazol-4-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 79313ノート

反応式

HRID 79313 の反応式
I[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[NH:11][C:12]([C:14]2[N:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]3=[N:16][CH:15]=2)=[O:13])[N:4]([CH2:23][C:24]2[CH:25]=[N:26][N:27]([CH2:29][C:30]3[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=3)[CH:28]=2)[N:3]=1.B(O)(O)O.F[C:43]([K])=[C:44](F)F.C(N(CC)CC)C.CO>C1COCC1.CC(O)C.[OH-].[OH-].[Pd+2]>[CH2:43]([C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[NH:11][C:12]([C:14]2[N:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]3=[N:16][CH:15]=2)=[O:13])[N:4]([CH2:23][C:24]2[CH:25]=[N:26][N:27]([CH2:29][C:30]3[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=3)[CH:28]=2)[N:3]=1)[CH3:44]

参加物

7

反応物 4

HCID 887MethanolHCID 8471TriethylamineHCID 67259250N-(3-iodo-1-((1-(4-methoxybenzyl)-1H-pyrazol-4-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamideHCID 178506051HCID 178506051、化合物

生成物 1

HCID 67260032N-(3-ethyl-1-((1-(4-methoxybenzyl)-1H-pyrazol-4-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide収率 64.6%

試薬・触媒・溶媒 2

HCID 9942167Palladium hydroxide触媒HCID 22597222Tetrahydrofuran 2-propanol溶媒

反応条件

温度
86 °C

実験手順

To N-(3-iodo-1-((1-(4-methoxybenzyl)-1H-pyrazol-4-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide (0.59 g, 0.98 mmol) in THF/IPA (1 mL/3 mL) was added trifluorovinylpotassium borate (0.20 g, 1.5 mmol), triethylamine (0.20 g, 2.0 mmol) and 1,1′-Bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (0.080 g, 0.098 mmol). The reaction mixture was heated at 86° C. and stirred for 5 hours. The reaction mixture was cooled to ambient temperature, concentrated under reduced pressure, and triturated with Et2O (30 mL) to give crude vinyl product, to which palladium hydroxide on carbon (20% wt, 0.27 mmol) and MeOH (20 mL) was added. The system was purged with N2 three times and a H2 balloon was applied to the system for 2 hours. The reaction mixture was filtered through Celite, washed with MeOH (20 mL), and concentrated to give the product (0.32 g). MS (ES+APCI) m/z=506 (M+H).

後処理

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. concentrationconcentrated under reduced pressure
  3. customtriturated with Et2O (30 mL)
  4. customto give crude vinyl product
  5. customThe system was purged with N2 three times
  6. waita H2 balloon was applied to the system for 2 hours
  7. filtrationThe reaction mixture was filtered through Celite
  8. washwashed with MeOH (20 mL)
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-b987d732b629444da24cc58412887f6f
出典データセット
uspto-grants-2014_09
特許番号
US08841455B2

反応ノート

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